Cartoonist Scott Adams shows off the new memoir detailing the numerous failures that he credits for his success.

Photo: Lea Suzuki, The Chronicle

Cartoonist Scott Adams shows off the new memoir detailing the...

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Scott Adams poses with a life-size cutout of his comic strip character Dilbert at the hilltop home he built in Pleasanton.

Photo: Lea Suzuki, The Chronicle

Scott Adams poses with a life-size cutout of his comic strip...

Image 3 of 4

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Scott Adams, cartoonist and author and creator of "Dilbert", poses for a portrait in his home office on Monday, January 6, 2014 in Pleasanton, Calif. Adams has published a new memoir "How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life".

When Scott Adams was growing up in the tiny Catskills ski resort town of Windham, N.Y., (population 2,000), he envisioned himself one day becoming a world-famous cartoonist like his idol Charles Schulz.

So at age 11 Adams sent cartoons to the Famous Artists Course for Talented Young People. A rejection letter soon followed: Adams was told the cutoff age was 12.

Though he was an inveterate doodler with a sarcastic bent, Adams shelved the cartooning dream. He focused instead on studying economics at Hartwick College near his home, where he started to dream about a different kind of success: creating and running a lucrative business.

Flash forward four decades, and Adams, 56, has managed to combine both dreams. Since 1989 he has been turning his ability to skewer the inanities of corporate management into gold with his highly successful comic strip Dilbert.

Inspired by the 16 years Adams spent working at Crocker National Bank and Pacific Bell in San Francisco, Dilbert is one of the most widely syndicated cartoons in the world. The three-panel strip about the bespectacled, cubicle-bound engineer with the curled-up tie runs in more than 2,000 newspapers in 70 countries and 25 languages.

"My problem looking back was that I had absolutely no role model or mentor in my small town to ask about how to go about achieving the success I wanted," says Adams. He has written an instructive and reflective new book detailing his improbable, failure-ridden road to success: "How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life" (Portfolio Penguin; $28).

Filled with unconventional, even counterintuitive, advice, "How to Fail" is equal parts memoir, self-help guide and business manual, throughout which Adams mines his career misadventures for applicable lessons in getting ahead.

Failures 'instructive'

"I've developed a reasonable, more statistical system for pursuing success, and the truth is my many failures were actually more instructive than the successes," Adams said recently from behind his desk in the spacious office where he creates Dilbert in the sprawling hilltop home in Pleasanton he built in 2009.

Adams' formula for success, in a nutshell, entails: scrapping goals; instead choosing projects based on the tangible skills you'll acquire on the job; and then using those skills again on future endeavors.

He likens his method of career advancement to "a venture capitalist's approach to investing. I've tried many business ideas assuming most would fail. Dilbert was my first idea that worked, but it was far from my first idea." He is currently involved with the startup CalendarTree, an online scheduler, now in beta.

"Think of each new skill you acquire as a doubling of your odds of success," Adams writes.

And, crucially, you need not be an expert at any one thing. "I'm a perfect example of the power of leveraging multiple mediocre abilities," he says. "My art skills are modest, nobody would say otherwise. I'm funny, but if I have a party in my own home I'm not the funniest guy in the room. I know just enough about business to have a context for the strip. But put all those together and it makes Dilbert special."

Why should anyone take work advice from a cartoonist? Because, Adams says, "I am a professional simplifier." Cartooning involves stripping out a situation's extraneous data to reveal the "absurd-yet-true core" of an idea. "Simplification comes as naturally to me as breathing does to some people."

He traces this strength back to the lessons he learned from his postal worker father and his mother, a factory worker who dreamed of being an artist.

"My mother had a philosophy that doing things the less efficient way was tantamount to a mortal sin."

Virginia Adams also passed on to her son a penchant for trying the unconventional. "She gave birth to my little sister while under hypnosis," says Adams, who is a trained hypnotist. (He says he "overtly used hypnosis techniques" while writing "How to Fail" - though, he says, "they will go undetected.")

Adams is a busy man. In addition to inking nine original comics every seven days (always at 5 a.m. - "It's got to be the first creative energy I spend of the day"), he is also head of the "Dilbert empire." The de facto multimedia conglomerate has included licensing and merchandise deals, book publishing ("How to Fail" is his ninth nonfiction, non-Dilbert book), animation, and a robust Web presence for Dilbert as well as Adams' popular and frequently provocative blog (dilbert.com/blog). He is also writing a script for a live-action Dilbert movie.

In conversation, Adams is both sincere and sarcastic. Humble and grandiose. With a quick mind - and wit - he has an entrepreneur's love of a new idea as well as a skeptic's refusal to take anything at face value.

Memorable failures

His quintessentially droll selling point for his new book? "I've failed at more things than anyone you've ever met."

His list of flat-lined inventions and entrepreneurial flops includes: a beginner's guide to meditation; a Velcro rosin bag that attached to tennis shorts; two early-'80s space-themed computer games; a major investment in the grocery-delivery service Webvan; a computer program to chart users' psychic abilities; two folded Pleasanton restaurants; and even the Dilberito, a 1999 attempt to mass-market a vitamin-fortified veggie burrito.

Among his biggest failures, Adams includes the seven years (1979-86) he spent as a teller (he was held up at gunpoint twice), computer programmer, budget analyst and supervisor at Crocker Bank.

He then spent nine years as a middle manager at Pacific Bell, earning his master's at UC Berkeley in the evenings. He revisited his doodling habit during tiresome meetings. The personalities he encountered at the phone company became the inspiration for many Dilbert characters.

Dilbert has kept its comedic edge through management fads and economic ups and downs. Despite evolving working environments such as flex schedules and the proliferation of social media, the strip has stayed relevant because of its everyman's outlook on the white-collar small-mindedness that can stifle personal achievement.

People don't change

Dilbert in recent years has incorporated "updates like people texting in meetings, Facebook gags, the cloud and telecommuting robots," says Adams. "But people stay just the same."

He dismisses the idea that trendy offices with open floor plans and on-site amenities have fundamentally changed the way employees interact with each other. The idiocy, laziness and ineffectiveness that are rampant in Dilbert's office - "those never change."

"Scott's work has stayed amazingly fresh all these years because he finds satire in reality, never resorting to cliche," says Sarah Gillespie, Adams' first comic editor, who discovered Dilbert among thousands of blind transmissions when Adams submitted samples to United Media in the late 1980s.

In preparation for the comic strip's 25th anniversary this year, Adams says he is contemplating modernizing Dilbert's look. "He could, possibly, lose his tie. I know engineers don't look like that anymore."

Adams was an early adapter to the Internet and made sure Dilbert was the first syndicated comic to run for free online. In 1993 he made the brilliant decision to put his e-mail address in every comic (it's still there). Workplace anecdotes from readers have been integral to the strip's evolution ever since.

"I hear from people all the time that if something is introduced at a company and it sounds like it could become a Dilbert cartoon, that alone is reason for a manager to hold back," says Adams. "No one wants to be the guy that gets 500 Dilbert cartoons flooding his e-mail because of something inane he just proposed."

In the past year Adams has started posting to Dilbert's Facebook and Twitter accounts, but "I wouldn't say I'm a fan of social media," he says. "Social media is too boring for a comic because it's mostly people staring at screens or taking pictures of food."

Adams says readers are most intrigued - and some dumbfounded - by two of his book's main tenets: "Goals are for losers" and "Passion is BS."

"Goals are OK," Adams says, "but they only work if you have a system - something you pursue on an ongoing basis. Losing 10 pounds is a goal, whereas learning to eat right is a system."

'Goals Gone Wild'

Some business management experts agree. "Goals can be incredibly motivating, but they can also motivate the wrong things," says Maurice Schweitzer, a professor at the Wharton School at the University of Pennsylvania. His 2009 paper "Goals Gone Wild" cautioned, like Adams, that excessive goal-setting can actually "degrade employee performance by narrowing focus."

As for passion being a requisite for success, Adams vehemently disagrees.

"I feel it might be the most damaging thing that has happened to this generation," says Adams. "I mean, there might be a whole lot of people who are not doing things, but are just waiting around for their passion to kick in."

He sees passion as a byproduct, rather than the source, of one's success. "I might have at any given time 10 business ideas, and when I see that one might have the potential to take on a life of its own, I start getting excited," he says. "My enthusiasm follows the success. Not vice versa."

Adams calls his post-college decision to leave rural New York for the Bay Area "an example of a system at work - moving from a small town with no opportunities to the land of opportunity."

He hated the East Coast cold so much that after getting trapped in his car in a snowstorm in 1979, Adams vowed that if he survived he'd buy a one-way ticket west. He slept on his brother's couch in Los Angeles before following a girlfriend to San Francisco.

In 2006, with much media attention, Adams got married to his girlfriend of two years, Shelly Miles, whom he met at his health club. When asked about his marriage or becoming a stepfather to Miles' two children, Adams declined to speak about his personal life.

People who know Adams only from laughing at their daily dose of Dilbert might be surprised to find a very different person on his popular blog. There Adams is a writer with a strong contrarian impulse and willingness to speak his mind on some controversial subjects, even if it means drawing considerable fire.

Favors assisted suicide

In a widely circulated November blog post Adams took a strident stand in favor of physician-assisted suicide that has caused some people - including this paper's columnist Debra Saunders - to take serious issue.

Written in the depths of grief and anger while his father, 86, was dying in hospice care in New York, Adams' post was an explosion of rage against laws preventing him from being able to "proactively end his (father's) suffering and let him go out with some dignity."

Adams fingered the government as responsible for the "torture" of his father, and wrote that he wanted politicians and voters who oppose assisted suicide "to die a long, horrible death."

Did he mean that?

"I do not regret the way I said it," says Adams. "It got a lot of attention."

Pew and Gallup polls in 2013 showed the public is almost evenly divided on the question of whether the law should permit physician-assisted suicide (currently legal in four states). Adams believes the numbers would tilt in favor of his position if the "question wasn't rigged."

"Instead of asking if doctors should be able to kill people sometimes, every poll on this from now on should ask: If you, your doctor and your family agree on a course of action for the end of your life, should the government have a veto on it? No one says yes to that. I have literally not heard one person who would take that side."

Adams believes his rough-edged blog post "got enough attention that I may have actually changed the debate going forward in this country. I contributed to something good. I believe that the better idea always wins."